Cyclohexanemethylamine → 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

HRID 1988393

반응식

HRID 1988393 반응식
CS(C1OC2C=C(OC3C=CN=C(C(NC)=O)C=3)C=CC=2N=1)=[O:3].C1(CN)CCCCC1.[CH:32]1([CH2:38][NH:39][C:40]2[O:41][C:42]3[CH:48]=[C:47]([O:49][C:50]4[CH:55]=[CH:54][N:53]=[C:52]([C:56](NC)=[O:57])[CH:51]=4)[CH:46]=[CH:45][C:43]=3[N:44]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:38][NH:39][C:40]2[O:41][C:42]3[CH:48]=[C:47]([O:49][C:50]4[CH:55]=[CH:54][N:53]=[C:52]([C:56]([OH:3])=[O:57])[CH:51]=4)[CH:46]=[CH:45][C:43]=3[N:44]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

참가 물질

4

반응물 3

HCID 76688CyclohexanemethylamineHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamideHCID 577255594-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

생성물 1

HCID 577255144-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

실험 절차

In Scheme 5, 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is aminated with cyclohexylmethanamine. The resulting 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is then hydrolyzed to form 4-[2-(cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid. 4-[2-(Cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid then reacts with benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate, tert-butyl carbazate, and triethyl amine to form 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide. 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide then reacts with trimethyl orthoformate to form a compound of the embodiments.

출처 및 근거

ORD 기록
ord-4320c0dd07eb421c9b124ff4e53a7d24
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553854B2

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